Multi-Component One-Pot Reactions for the Synthesis of Spirooxindole-pyrano[2,3-c]pyrazole Derivatives

被引:2
|
作者
Feng, Jun [1 ]
Ablajan, Keyume [1 ]
Ma, Xiabing [1 ]
Li, Wenbo [1 ]
Obul, Mamateli [1 ]
机构
[1] Xinjiang Univ, Coll Chem & Chem Engn, Minist Educ & Xinjiang Uyghur Autonomous Reg, Key Lab Oil & Gas Fine Chem, Urumqi 830046, Peoples R China
基金
中国国家自然科学基金;
关键词
spirooxindole; multi-component reaction; one-pot synthesis; pyrano[2,3-c]pyrazole; REGIOSELECTIVE SYNTHESIS; L-PROLINE; EFFICIENT; CYCLIZATION; CONVENIENT; ACCESS; FACILE;
D O I
10.6023/cjoc201507011
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient strategy for the one-pot synthesis of multi-substituted spirooxindol-pyrano[2,3-c]pyrazole derivatives was developed. The product formed in good yield from the reaction of acetylenedicarboxylate, hydrazine, isatin, and (E)-1-methylthio-1-methylamino-2-nitroethylene in the presence of Et3N catalyst. This simple and convenient method could also be used to prepare similar types of product.
引用
收藏
页码:222 / 228
页数:7
相关论文
共 49 条
  • [1] The Michael addition of indoles to α,β-unsaturated ketones catalyzed by CeCl3•7H2O-NaI combination supported on silica gel
    Bartoli, G
    Bartolacci, M
    Bosco, M
    Foglia, G
    Giuliani, A
    Marcantoni, E
    Sambri, L
    Torregiani, E
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11): : 4594 - 4597
  • [2] New thiophene analogues of kenpaullone:: synthesis and biological evaluation in breast cancer cells
    Brault, L
    Migianu, E
    Néguesque, A
    Battaglia, E
    Bagrel, D
    Kirsch, G
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (08) : 757 - 763
  • [3] Recent Advances on Multicomponent Reactions Based on the Transamination Process of Electron Deficient Enamines
    Cao, Shuo
    Jing, Yanfeng
    Liu, Yunyun
    Wan, Jieping
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (05) : 876 - 885
  • [4] Efficient one-pot synthesis of spiro[indoline-3,4′-pyrazolo[3,4-e][1,4]thiazepine]dione via three-component reaction
    Chen, Hui
    Shi, Daqing
    [J]. TETRAHEDRON, 2011, 67 (31) : 5686 - 5692
  • [5] Organocatalytic Synthesis of Spiro[pyrrolidin-3,3′-oxindoles] with High Enantiopurity and Structural Diversity
    Chen, Xiao-Hua
    Wei, Qiang
    Luo, Shi-Wei
    Xiao, Han
    Gong, Liu-Zhu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (38) : 13819 - 13825
  • [6] Christoffers J, 1998, EUR J ORG CHEM, V1998, P1259
  • [7] Efficient microwave enhanced regioselective synthesis of a series of benzimidazolyl/triazolyl spiro [indole-thiazohdinones] as potent antifungal agents and crystal structure of spiro[3H-indole-3,2′-thiazolidine]-3′(1,2,4-triazol-3-yl)-2,4′(1H)-dione
    Dandia, A
    Singh, R
    Khaturia, S
    Mérienne, C
    Morgant, G
    Loupy, A
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (07) : 2409 - 2417
  • [8] Total synthesis of spirotryprostatin A, leading to the discovery of some biologically promising analogues
    Edmondson, S
    Danishefsky, SJ
    Sepp-Lorenzino, L
    Rosen, N
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (10) : 2147 - 2155
  • [9] Electrocatalytic multicomponent assembling of isatins, 3-methyl-2-pyrazolin-5-ones and malononitrile: facile and convenient way to functionalized spirocyclic [indole-3,4'-pyrano[2,3-c]pyrazole] system
    Elinson, Michail N.
    Dorofeev, Alexander S.
    Miloserdov, Fedor M.
    Nikishin, Gennady I.
    [J]. MOLECULAR DIVERSITY, 2009, 13 (01) : 47 - 52
  • [10] 4-Dimethylaminopyridine-catalyzed multi-component one-pot reactions for the convenient synthesis of spiro[indoline-3,4′-pyrano [2,3-c]pyrazole] derivatives
    Feng, Jun
    Ablajan, Keyume
    Sali, Ahat
    [J]. TETRAHEDRON, 2014, 70 (02) : 484 - 489